There are many reasons for this including tax and liability issues.

HAVE a move out check list cost sheet in you policy packet that covers the cost to remove the nicotine,, 200 bucks a room to prep and seal.. and take photos of walls,, have washed so you can see what the issue is, if questioned later..8  NO smoking policy is best way to go.. 

My first step to answering my question "how can I make a deal and succeed without having to worry about financial issues?"

That would be the safest.A family trust will resolve some of the ambiguity and relieve the probate issue.  

Don't really know what that means or entails so I need to research that.Has anyone ever dealt with any of these issues?

If its the foundation issues then I would seek out an engineer or foundation company to get bids.

I have since refinanced my properties into a commercial portfolio loan and the issue isn't as relevant.

I own a rental out in Long Island, and the issue is also the prices are sky high. 

Trash,, is a constant issue,, notify tenants,, properly dispose of,, add containers if needed.. let tenants know any trash not put in cans they will be fined,, I've dug thru trash found envelopes to tenants,,taken screen shot and they get 25.00 fine for not getting it in the bin.... don't be surprised if neighbor is one to call that complaint in.. 3.

Anyone else ever dealt with an issue like this?